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Our birth-class instructor had said it in passing. Now I understood what she meant.

Peter and I stood in the cabin of our Cal 25, a once-sprightly, now put-out-to-pasture sloop and struggled to tune the spit-crackling marine radio. We'd arrived by car at Shilshole Bay Marina in Seattle the night before and slept on board, nestled below the bluffs. Now, as I looked through the cabin's companionway, the new day was not promising. Metal halyards, strung to the forest of aluminum masts, snapped and clanged in the fitful gusting wind, like an Indonesian gamelan orchestra.

We found the NOAA channel.

"Small craft advisory in effect until tomorrow night. Wind waves two to four feet...Southwest winds 15 to 25 knots...rain..."

None of this would really have mattered—in fact I like getting stuck, having a guilt-free excuse to lounge and read—except that the boat was a share. Our allotted five days were being eaten away.

Not to mention, our one-year-old daughter, Molly, was kicking around our feet, adding a whole new dimension of tension. Generally, in past adventures, Peter and I had managed to strike a pretty good balance between risk and safety. At least we'd survived. But now I imagined our cherubic child plummeting like a bowling ball down into the bone-aching depths of the Sound. I tried to reign in the horrific thoughts that began whipping through my mind. I could recognize them as improbable, but that didn't keep them from coming. We decided to wait until late morning. Maybe something would change.

Nothing changed. There are 1,400 boat slips at Shilshole. Not one boat budged.

With Molly encased in pile and stuffed into a kid pack, we climbed the stone breakwater that shelters huddled boats from the open sound. We stared across white caps to Bainbridge Island on the other side.

"I think it's something like 23 nautical miles to Langley," Peter said. "Maybe we could try the first leg and see how it feels."

In general, we've found the best way to gauge risk is to get as close to it as you can, whether that means figuratively or literally—by talking to someone else in a similar situation or by carefully nosing in yourself. We decided to nose in. But first we made a safety plan.

Our original goal had been a five-day, 70-mile trip. We'd zigzag our way north to Anacortes, meet up with my dad, then tack our way west to Friday Harbor on San Juan Island where we'd hand the boat over to its other owners.

Our new plan was to venture out one leg at a time and reassess. We jury-rigged a harness for Molly, tying one end of a rope around her waist and the other end to a cleat. (There are no doubt actual harnesses for this purpose, but we didn't have one.) If somehow Molly came loose and was thrown overboard, I was to plunge in after her, while Peter tried to bring the boat around. I'd done some long-distance swimming in the Sound and knew too well the feeling of petrifying cold. It starts in your extremities and colonizes your body like an ice cube freezing from the outside in. But I was a strong swimmer and Peter was better with the boat. If we felt we were getting in over our heads we could always turn back.

Returning to the boat, we started the motor. We tentatively putted our way out to the entrance. We peaked around the end of the breakwater. Creeping out into the open, we were quickly swept into a rising, falling, rocking, rolling immensity of water and sky. Sliding on a wet deck, I frantically raised the mainsail in an attempt to stabilize us. This helped. I opened a hatch and looked down below. We'd wedged Molly between pillows in the V-berth in the bow, so she wouldn't slide every time we rolled. Far from panicking, she'd simply fallen asleep.

It struck me, in retrospect, that without the anxiety of "what ifs?" and the dire imaginings of worst-case scenarios, the rollicking ride was a total blast. I remembered that as a child, eyes closed, I'd spin and spin, drunkenly staggering until I fell, loving the physical feeling of careening out of control. When had I lost that? I guess when I'd come to the realization that sometimes bad things happen when you're out of control. Things you can't take back. So then comes the risk assessment. But for Molly, at one, there was no assessing. She'd entrusted her parents with that. We were feeling the weight of the responsibility.

Several strenuous hours later we sailed into the dock at Langley, a charming town of about a thousand on the south end of Whidbey Island. Peter and I felt exhilarated, relieved, empowered, triumphant, and glad to stop. Molly, oblivious, was cheerful as ever. Springing off the boat onto the rooted planks of the pier, Peter said he'd never been so grateful for land and shelter.

This is why it's worth taking a risk, albeit a calculated one. For the chance to relish what we have, spurred by the recognition that for that moment we could have lost it; and for another small triumph in our battle against fear, another notch in our quest of a broader world. Of course, everyone has a different tolerance for risk, and fear is an important survival response. But sometimes it's worth pushing back.